Hydrochloric Acid → HCID 178522100, compound

HRID 2109033Notes

Reaction equation

HRID 2109033 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([C:20](OC)=[O:21])=[CH:16][CH:17]=3)[C:12]=2[NH:24][C:25]([C@H:27]2[CH2:32][CH2:31][C@H:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C:34]3=[O:39])[CH2:29][CH2:28]2)=[O:26])=[O:10])=[N:6][CH:7]=1.[BH4-].[Li+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([CH2:20][OH:21])=[CH:16][CH:17]=3)[C:12]=2[NH:24][C:25]([C@H:27]2[CH2:28][CH2:29][C@H:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C:34]3=[O:39])[CH2:31][CH2:32]2)=[O:26])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 178497416HCID 178497416, compound

Product 1

HCID 178522100HCID 178522100, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylate (300 mg) obtained in Example 39 is suspended in tetrahydrofuran (15 ml), and thereto is added lithium borohydride (24 mg) under ice-cooling, and the mixture is stirred at room temperature for 20 hours. To the reaction solution is poured 10% hydrochloric acid under ice-cooling, and the mixture is stirred at room temperature for 15 minutes. The reaction solution is alkalified with saturated aqueous sodium hydrogen carbonate solution, and then extracted with ethyl acetate. The organic layer is washed with saturated brine and dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1). The resulting solid is suspended in diethyl ether-n-hexane and collected by filtration to give the title compound (80 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature for 15 minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1)
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-938289ae0b26494da3aa6b71620f331d
Source dataset
uspto-grants-2009_04
Patent number
US07514449B2

Reaction notes

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